Tim thinks wearing a Cinderella dress during March Madness is good luck, so he refuses to take it off in hopes his alma mater will win. Also, Greg fantasizes about what to write in a birthday card for his boss, Tyler goes to prom and must withstand unsolicited advice from his parents and grandparents, and Jen sets Matt up on a blind date with her coworker, Dougie.

The first season concludes with John and Joan revealing a shocking secret they've kept from their kids for 35 years. Also, Greg quits his job after creating a public funding campaign for his own invention. Heather and Tim try to make up for missing Samantha's Student of the Month Ceremony at school, and Matt's plan to make a big announcement at his and Colleen's book party keeps getting delayed.

When Sophia feels like she is no longer the cutest kid in the Short family, she tries frantically to regain her status. Also, Joan gives Jen a beautiful necklace, forgetting she already gave it to Heather for her Sweet 16, and now she has to get it back; Greg tries to fit in with his new young coworkers but takes things too far; and Colleen and Tim bond when he helps her administer the hormone injections for her IVF treatment.